Problem: Predict the product(s).

FREE Expert Solution
FREE Expert Solution

We’re being asked to determine the products of the given reaction.



Recall that alkenes are converted to alcohols via oxymercuration-reduction:



This occurs in three steps:

(1) electrophilic addition – the alkene attacks Hg(OAc)2, forming the cyclic mercurinium ion. Since a cyclic intermediate is formed, rearrangement is not possible for this reaction.


(2) nucleophilic attack – water attacks the cyclic mercurinium ion. This follows Markovnikov’s rule, where water attacks the more-substituted carbon. The stereochemistry of this reaction is anti, where –OH and –HgOAc will be trans to each other.


(3) reduction – NaOH and NaBH4 react with the intermediate to form the alcohol.


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Predict the product(s).

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What scientific concept do you need to know in order to solve this problem?

Our tutors have indicated that to solve this problem you will need to apply the Oxymercuration concept. You can view video lessons to learn Oxymercuration. Or if you need more Oxymercuration practice, you can also practice Oxymercuration practice problems.